4-chloro-N-(3-morpholinopropyl)nicotinamide | 1202770-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-chloro-N-(3-morpholinopropyl)nicotinamide
• 英文别名: 4-chloro-N-(3-morpholin-4-ylpropyl)pyridine-3-carboxamide
• CAS: 1202770-39-5
• 化学式: C₁₃H₁₈ClN₃O₂
• mdl: MFCD23538696
• 分子量: 283.758
• InChiKey: XYKBQKHBJFXZSH-UHFFFAOYSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  466.2±45.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(3-氨丙基)吗啉 、 4-氯烟酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到4-chloro-N-(3-morpholinopropyl)nicotinamide
  参考文献：
  名称：

  Design of novel nicotinamides as potent and selective monoamine oxidase a inhibitors

  摘要：

  A series of N-(2-morpholinoethyl)nicotinamide (1-13) and N-(3-morpholinopropyl)nicotinamide derivatives (14-26) have been designed, synthesized and evaluated in vitro for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. Most of these synthesized compounds proved to be potent, and selective inhibitors of MAO-A rather than of MAO-B. 5-Chloro-6-hydroxy-N-(2-morpholinoethyl)nicotinamide (13) displayed the highest MAO-A inhibitory potency (IC50 = 0.045 mu M) and a good selectivity. 2-Bromo-N-(2-morpholinoethyl)nicotinamide (3) was the most potent MAO-B inhibitor with the IC50 value of 0.32 mu M, but it was not selective. Molecular dockings of compound 13 were performed in order to give structural insights regarding the MAO-A selectivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.065

文献信息

• [EN] ALKYNYL ALCOHOLS AS KINASE INHIBITORS<br/>[FR] ALCOOLS D'ALCYNYLE UTILISÉS COMME INHIBITEURS DE KINASES
  申请人：AMGEN INC

  公开号：WO2009158011A1

  公开（公告）日：2009-12-30

  Selected compounds are effective for prophylaxis and treatment of inflammation and inflammatory disorders, such as NIK-mediated disorders. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, inflammation and the like.

  选定的化合物对预防和治疗炎症和炎症性疾病，如NIK介导的疾病，具有有效性。该发明涵盖了新颖的化合物、类似物、前药及其药用可接受的盐，以及用于预防和治疗涉及炎症等疾病和其他疾病或病症的药物组合物和方法。
• ALKYNYL ALCOHOLS AS KINASE INHIBITORS
  申请人：Chen Guoqing

  公开号：US20110086834A1

  公开（公告）日：2011-04-14

  Selected compounds are effective for prophylaxis and treatment of inflammation and inflammatory disorders, such as NIK-mediated disorders. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, inflammation and the like.

  所选化合物对于预防和治疗炎症和炎症性疾病（如NIK介导的疾病）有效。本发明涵盖新的化合物、类似物、前药和其药学上可接受的盐、制药组合物和预防和治疗涉及炎症等疾病和其他疾病或病症的方法。
• Design of novel nicotinamides as potent and selective monoamine oxidase a inhibitors
  作者：Lei Shi、Ying Yang、Zi-Lin Li、Zhen-Wei Zhu、Chang-Hong Liu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2009.12.065

  日期：2010.2

  A series of N-(2-morpholinoethyl)nicotinamide (1-13) and N-(3-morpholinopropyl)nicotinamide derivatives (14-26) have been designed, synthesized and evaluated in vitro for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. Most of these synthesized compounds proved to be potent, and selective inhibitors of MAO-A rather than of MAO-B. 5-Chloro-6-hydroxy-N-(2-morpholinoethyl)nicotinamide (13) displayed the highest MAO-A inhibitory potency (IC50 = 0.045 mu M) and a good selectivity. 2-Bromo-N-(2-morpholinoethyl)nicotinamide (3) was the most potent MAO-B inhibitor with the IC50 value of 0.32 mu M, but it was not selective. Molecular dockings of compound 13 were performed in order to give structural insights regarding the MAO-A selectivity. (C) 2010 Elsevier Ltd. All rights reserved.